Potassium Carbonate → 4-chloro-2-iodo O-crotyl phenol

HRID 22743

Reaction equation

HRID 22743 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([I:9])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:16](Br)[CH:17]=[CH:18][CH3:19]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:16][CH:17]=[CH:18][CH3:19])=[C:4]([I:9])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1224142-Butene, 1-bromo-HCID 6202344-Chloro-2-iodophenol

Product 1

HCID 698740424-chloro-2-iodo O-crotyl phenolYield 95.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-chloro-2-iodo phenol (5.11 mmol, 1.3 g) in DMF (40 mL) and potassium carbonate (10 mmol, 1.4 g) was added crotyl bromide (10.2 mmol, 1.6 g) and the reaction mixture was stirred at room temperature for one hour. The reaction was quenched with H2O (100 mL) and extracted with EtOAc (2×50 mL). The EtOAc layer was collected, dried, filtered and the filtrate was evaporated to obtain 4-chloro-2-iodo O-crotyl phenol (94%, 1.5 g).

Workup

  1. customThe reaction was quenched with H2O (100 mL)
  2. extractionextracted with EtOAc (2×50 mL)
  3. customThe EtOAc layer was collected
  4. customdried
  5. filtrationfiltered
  6. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-f5692c16398741cabed348cb70f8d640
Source dataset
uspto-grants-2005_02
Patent number
US06849629B2

Linked notes

Loading…